I think you need to think more about what you want. I see you want a ski/pleasure boat. IMO there is no such thing. they don't really perform either very good. Yes, you can ski behind them but its not the same as a real ski boat. now if you want to pull a tube and ride around the hybrids are fine. and you do get more options for the money...but if want to do some skiing and or wakeboarding get a inboard...I bought my last 2 boats on boattrader.com
above ^ is all excellent advice.
write down every way you plan to use your boat and put percentages to every use adding up to 100% to figure what style of boat will match your needs best
Typically you will learn what type of boater you are once you begin boating with your own boat , previously you have done what people that invited you out with them do with their boats.
plan on hitting the nail on the head with your second boat not your first ! make sure whatever you buy is a popular boat that will hold a good resale value so you get the majority of what you paid back in a few years when you are ready to buy a boat suited to your specific needs.
Maybe something between 18-20 feet with either a 4.3 efi or 5.0/5.7 efi , avoid new because the depriciation will kill you when you buy your next boat as most new boaters do pretty quickly - if you get into water sports you will end up wanting an inboard either direct drive if skiing is your thing or v-drive if wakeboarding, wakeskating ,wakesurfing, or sky skiing. If you spend more time cruising you will end up in an inboard outboard ( stern drive) fishing in lakes typically outboard but some use IO's
volvo penta ,mercruiser, Indmar ,Pcm all use gm engines and all are easily serviceable most anywhere
in this day and age stay away from carb boats they are difficult to resell as are underpowered boats.
Every boat I put under contract I write on the deal subject to water test and visual inspection - give yourself the opportunity to see & drive any boat before closing any deal even if it is 10 states away. You can also pay an independent boat surveyor to check out a boat on your behalf allthough a friend into boats and a good eye goes a long ways.
efi boats can be hooked up to a scan tool to verify engine hours ,past codes , how many hours in what rpm ranges ,etc.. anyone really looking to earn your business should be willing to let you spend 15 minutes scanning it with a tech - i do it all the time
I have been selling boats for 8 years and boating much longer
I typically have between 100-150 boats listed on boat trader and it is amazing how it has helped me sell boats literally all over the world
I started with an 18 foot sea ray with a 5.0 mercruiser got into wakeboarding and have owned a bunch of Malibu watersports boats since